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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-23 01:33:43 UTC
Update Date2022-03-07 02:49:31 UTC
HMDB IDHMDB0006351
Secondary Accession Numbers
  • HMDB0006207
  • HMDB06207
  • HMDB06351
Metabolite Identification
Common NameVaccenyl carnitine
DescriptionVaccenyl carnitine is a long-chain acyl fatty acid derivative ester of carnitine. Long-chain acyl fatty acid derivatives accumulate in the cytosol and serum of patients suffering of mitochondrial carnitine palmitoyltransferase II (CPT II, EC 2.3.1.12) deficiency, the most common inherited disorder of lipid metabolism in adults. carnitine palmitoyltransferase II deficiency is an autosomal recessive disorder of fatty acid metabolism presenting as two clinical phenotypes: (i) a severe infantile hepatocardiomuscular form and (ii) a milder adult muscular form. Energy production from long-chain fatty acids (LCFAs) requires the transport of LCFAs into the mitochondrial matrix. This transport is carnitine-dependent and involves translocation machinery. mitochondrial fatty acid oxidation disorders cause hypoglycaemia, hepatic dysfunction, myopathy, cardiomyopathy and encephalopathy. Patients with end-stage renal disease (ESRD) undergoing long-term haemodialysis exhibit elevated acylcarnitine concentrations. (PMID: 11999976 , 10682306 , 15025677 , 16168195 ).
Structure
Data?1582752382
Synonyms
ValueSource
O-(trans-Vaccenoyl)-D-carnitineChEBI
O-[(e)-Vaccenoyl]-D-carnitineChEBI
Acylcarnitine C18:1HMDB
R-(11E Octadecenoyl) carnitineHMDB
Chemical FormulaC25H47NO4
Average Molecular Weight425.654
Monoisotopic Molecular Weight425.350508997
IUPAC Name(3S)-3-[(11E)-octadec-11-enoyloxy]-4-(trimethylazaniumyl)butanoate
Traditional Name(3S)-3-[(11E)-octadec-11-enoyloxy]-4-(trimethylammonio)butanoate
CAS Registry NumberNot Available
SMILES
CCCCCC\C=C\CCCCCCCCCC(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C
InChI Identifier
InChI=1S/C25H47NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-25(29)30-23(21-24(27)28)22-26(2,3)4/h10-11,23H,5-9,12-22H2,1-4H3/b11-10+/t23-/m0/s1
InChI KeyHOAMADDCQBUDDY-YSESTWPTSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentAcyl carnitines
Alternative Parents
Substituents
  • Acyl-carnitine
  • Dicarboxylic acid or derivatives
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid salt
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.5e-06 g/LALOGPS
logP2ALOGPS
logP2.56ChemAxon
logS-7.9ALOGPS
pKa (Strongest Acidic)4.22ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.43 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity147.4 m³·mol⁻¹ChemAxon
Polarizability53.26 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+220.67630932474
DeepCCS[M-H]-217.41630932474
DeepCCS[M-2H]-251.66630932474
DeepCCS[M+Na]+228.17330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Vaccenyl carnitineCCCCCC\C=C\CCCCCCCCCC(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C3140.8Standard polar33892256
Vaccenyl carnitineCCCCCC\C=C\CCCCCCCCCC(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C2620.5Standard non polar33892256
Vaccenyl carnitineCCCCCC\C=C\CCCCCCCCCC(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C2889.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Vaccenyl carnitine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vaccenyl carnitine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaccenyl carnitine 10V, Positive-QTOFsplash10-05r3-0953800000-10c117f27cdeca6b78e82019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaccenyl carnitine 20V, Positive-QTOFsplash10-0006-1920000000-454f3fd140a9f3a759522019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaccenyl carnitine 40V, Positive-QTOFsplash10-006x-4940000000-cf06ad95e45d27992e002019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaccenyl carnitine 10V, Negative-QTOFsplash10-00di-1031900000-560a56638a8a770c68862019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaccenyl carnitine 20V, Negative-QTOFsplash10-00yi-1179400000-ed01fc9b8478ba25da722019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaccenyl carnitine 40V, Negative-QTOFsplash10-06s6-5090000000-92221a20e063037e4db42019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaccenyl carnitine 10V, Positive-QTOFsplash10-004i-0000900000-c76c8c1a67e6b24de5c12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaccenyl carnitine 20V, Positive-QTOFsplash10-002r-9000500000-4902a8769b2895518a152021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaccenyl carnitine 40V, Positive-QTOFsplash10-000i-9000000000-e9262cbaff8cb4ad0ba62021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023900
KNApSAcK IDNot Available
Chemspider ID64808356
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2614385
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477830
PDB IDNot Available
ChEBI ID136372
Food Biomarker OntologyNot Available
VMH IDOCDECECRN
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Reuter SE, Evans AM, Faull RJ, Chace DH, Fornasini G: Impact of haemodialysis on individual endogenous plasma acylcarnitine concentrations in end-stage renal disease. Ann Clin Biochem. 2005 Sep;42(Pt 5):387-93. [PubMed:16168195 ]
  2. Gempel K, Kiechl S, Hofmann S, Lochmuller H, Kiechl-Kohlendorfer U, Willeit J, Sperl W, Rettinger A, Bieger I, Pongratz D, Gerbitz KD, Bauer MF: Screening for carnitine palmitoyltransferase II deficiency by tandem mass spectrometry. J Inherit Metab Dis. 2002 Feb;25(1):17-27. [PubMed:11999976 ]
  3. Shen JJ, Matern D, Millington DS, Hillman S, Feezor MD, Bennett MJ, Qumsiyeh M, Kahler SG, Chen YT, Van Hove JL: Acylcarnitines in fibroblasts of patients with long-chain 3-hydroxyacyl-CoA dehydrogenase deficiency and other fatty acid oxidation disorders. J Inherit Metab Dis. 2000 Feb;23(1):27-44. [PubMed:10682306 ]
  4. Spiekerkoetter U, Tokunaga C, Wendel U, Mayatepek E, Exil V, Duran M, Wijburg FA, Wanders RJ, Strauss AW: Changes in blood carnitine and acylcarnitine profiles of very long-chain acyl-CoA dehydrogenase-deficient mice subjected to stress. Eur J Clin Invest. 2004 Mar;34(3):191-6. [PubMed:15025677 ]